Pompey’s previous high-profile penalty shoot-outs have not ended well.
There was that Villa Park defeat in the FA Cup in 1992 and then a Community Shield loss to Manchester United at Wembley in 2008.
But it proved to be third time luck against Sunderland, as Kenny Jackett’s side held their nerve to lift the Checkatrade Trophy.
Gareth Evans, Brett Pitman, Jamal Lowe and Lee Brown all tucked their efforts away, while Craig MacGillivray denied Lee Cattermole.
That gave Oli Hawkins the opportunity to seal victory in front of the jubilant Pompey fans and Jackett was delighted with the efforts of his players.
The Blues boss said: “We found a way to win in the shoot-out with five excellent penalties and a terrific save from Craig.
“It was something we had practiced and it’s the old adage about not changing your mind once its made up.
“We knew the players who were comfortable taking them and then those who feel both physically and mentally strong enough.
“Brett and Gareth have them before and Jamal was very confident – so there was our first three. Lee will always put himself forward as well.
"We knew the players who were comfortable taking them and then those who feel both physically and mentally strong enough."
“It’s all about the forwards after that because you want people with experience of putting the ball in the net and Oli took a great penalty. I was really pleased for him.”
Pompey recovered from a slow start and Nathan Thompson cancelled out Aiden McGeady’s opener to take the tie to extra-time.
Lowe looked to have won an absorbing contest with a glorious lob late on, but McGeady struck again before the Blues ultimately triumphed.
Jackett said: “I thought it was a great advert for League One football and both clubs had fantastic support to generate that atmosphere.
“It was a soft free-kick and then a deflection for the opening goal, but I did think Sunderland were the better team in the first half and deserved their lead.
“From that point on, however, we were on top and did very well throughout the second period and in extra-time.
“We’ll enjoy it and want to use the result as a springboard so we can finish the season strongly – it’s all ahead of us now.
“We don’t want to be complacent because winning promotion is no easy matter and we have to keep persevering.”